5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-indenyl-3-acetic acid is a known compound having anti-inflammatory activity described in U.S. Pat. No. 3,654,349. Previously, this compound has been prepared by condensing an appropriately substituted benzaldehyde with an acetic acid ester in a Claisen reaction or with an alpha-halogenated propionic acid ester in a Reformatsky reaction. The resulting unsaturated ester was reduced and hydrolyzed to give a beta-aryl propionic acid which is subsequently ring closed to form the indanone. The aliphatic side chain was then introduced by a Reformatsky or Wittig reaction and the 1-substituent was introduced into the resultant indenyl acetic acid or ester by reacting said acetic acid derivative with an aromatic aldehyde or ketone of the desired structural formula and dehydrating to form the desired indenyl acetic acid.
It is an object of this invention to provide new processes of preparing 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-indenyl-3-acetic acid from starting materials with the acetic acid side chain already incorporated.